{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T00:27:40Z","timestamp":1760660860609,"version":"build-2065373602"},"reference-count":27,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2022,3,24]],"date-time":"2022-03-24T00:00:00Z","timestamp":1648080000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003321","name":"Queen's University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003321","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Labelled Comp Radiopharmac"],"published-print":{"date-parts":[[2022,5,30]]},"abstract":"<jats:p>Baricitinib, typically applied as a treatment for rheumatoid arthritis, has recently attracted the attention of clinicians and researchers as a potential treatment for COVID\u201019. Naturally, there has been a need for the preparation of the isotope\u2010labelled analogue of baricitinib to probe the pharmacokinetics of baricitinib in this new role. As such, we have developed a simple synthetic route to deuterated [<jats:sup>2<\/jats:sup>H<jats:sub>5<\/jats:sub>]baricitinib, facilitating its formation over four steps and in a 29% overall yield based on starting [<jats:sup>2<\/jats:sup>H<jats:sub>5<\/jats:sub>]ethanethiol (19% if we start with [<jats:sup>2<\/jats:sup>H<jats:sub>5<\/jats:sub>]bromoethane instead). A critical component of the overall process involves the synthesis of [<jats:sup>2<\/jats:sup>H<jats:sub>5<\/jats:sub>]ethanesulfonyl chloride, and we describe in detail the two routes that were explored to optimize this step.<\/jats:p>","DOI":"10.1002\/jlcr.3969","type":"journal-article","created":{"date-parts":[[2022,3,11]],"date-time":"2022-03-11T22:18:06Z","timestamp":1647037086000},"page":"156-161","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of [<sup>2<\/sup>H<sub>5<\/sub>]baricitinib via [<sup>2<\/sup>H<sub>5<\/sub>]ethanesulfonyl chloride"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2919-6962","authenticated-orcid":false,"given":"Ross D.","family":"Jansen\u2010van Vuuren","sequence":"first","affiliation":[{"name":"Department of Chemistry Queen's University  Kingston Ontario Canada"},{"name":"Faculty of Chemistry and Chemical Technology University of Ljubljana  Ljubljana Slovenia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rahul","family":"Vohra","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Business Development Sussex\u2010Research Lab Inc.  Ottawa Ontario Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,3,24]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1473-3099(20)30132-8"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S2213-2600(21)00331-3"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1093\/cid\/ciaa879"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/phar.2438"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.abe4724"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.1818"},{"key":"e_1_2_8_8_1","first-page":"1","article-title":"Synthesis of carbon\u201014 and stable isotope labeled Censavudine","author":"Burrell RC","year":"2022","journal-title":"J Label Compd Radiopharm"},{"key":"e_1_2_8_9_1","unstructured":"TungRD.Deuterated baricitinib. US10842792B2;2020."},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.3184\/174751916X14569294811333"},{"key":"e_1_2_8_11_1","unstructured":"RodgersJD MaduskuieSSTP WangH et al.Heteroaryl substituted pyrrolo[2 3\u2010b]pyridines and pyrrolo[2 3\u2010b]pyrimidines as Janus kinase inhibitors. US20070135461;2007."},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03075"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339675"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra42932f"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo070907g"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)02853-8"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA26944C"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1316890"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1992.1483"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01186a082"},{"key":"e_1_2_8_21_1","unstructured":"RodgersJD ShepardS LiY\u2010L ZhouJ LiuP MeloniD XiaM.Azetidine and cyclobutane derivatives as JAK inhibitors. WO2009114512 A1;2009."},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00355a013"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja027822b"},{"key":"e_1_2_8_24_1","unstructured":"FriedmanPA FridmanJS LuchiME WilliamsWV.Janus kinase inhibitors for treatment of dry eye and other eye related diseases. WO2010039939;2010."},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570240328"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1080\/15257771003612847"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-075067571-0\/50007-7"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1139\/v76-067"}],"container-title":["Journal of Labelled Compounds and Radiopharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.3969","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/jlcr.3969","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.3969","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T15:55:56Z","timestamp":1760630156000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jlcr.3969"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,3,24]]},"references-count":27,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2022,5,30]]}},"alternative-id":["10.1002\/jlcr.3969"],"URL":"https:\/\/doi.org\/10.1002\/jlcr.3969","archive":["Portico"],"relation":{},"ISSN":["0362-4803","1099-1344"],"issn-type":[{"type":"print","value":"0362-4803"},{"type":"electronic","value":"1099-1344"}],"subject":[],"published":{"date-parts":[[2022,3,24]]},"assertion":[{"value":"2022-01-25","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-03-03","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-03-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}